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Diisopropylethylamine → tert-Butyl 4-[(4-iodopyridin-2-yl)carbonyl]-1,4-diazepane-1-carboxylate

HRID 1172795
Notes
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Reaction equation

HRID 1172795 reaction equation
[I-].[C:2]([C:5]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][NH+:6]=1)([OH:4])=O.[N:12]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[I:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([C:2]([N:15]2[CH2:16][CH2:17][CH2:18][N:12]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][CH2:14]2)=[O:4])[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 686869452-Carboxy-4-iodopyridinium iodide

Product 1

HCID 86633425tert-Butyl 4-[(4-iodopyridin-2-yl)carbonyl]-1,4-diazepane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-carboxy-4-iodopyridinium iodide (1 eq) in DMF were added tert-butyl 1-homopiperazinecarboxylate (2.05 eq), HBTU (2.05 eq) and DIPEA (2.05 eq) and the mixture was stirred overnight at RT. The reaction mixture was diluted with DCM and washed with 0.5N HCl solution and brine. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The resulting crude was used as such in the next step without purification. MS (ES) C16H22IN3O3 requires: 431, found: 432 (M+H)+.

Workup

  1. washwashed with 0.5N HCl solution and brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customwithout purification

Sources & evidence

ORD record
ord-20e78083fe19446d8fb5925cfeba920d
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07834015B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes